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Cheshire Vacation Packages

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Cheshire Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Lodges At Cresthaven

Lodges At Cresthaven

4 out of 5
Price was $641, price is now $471 per person
$471
per person
Nov 19 - Nov 22
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
Book a stay at this beach lodge in Lake George. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Lake George Steamboat Company and Fort William Henry Museum are located nearby.
Always great can’t wait to return

Reviewed on Sep 3, 2026

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

3.5 out of 5
Price was $1,199, price is now $842 per person
$842
per person
Nov 10 - Nov 17
found 1 day ago
Roundtrip flight included
Houston (HOU) to Albany (ALB)
Stay at this B&B in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the comfy rooms in our reviews. Popular attractions Tanglewood Music Center and Lenox Library are located nearby.

The Whitlock

The Whitlock

2 out of 5
Price was $1,037, price is now $746 per person
$746
per person
Nov 10 - Nov 17
found 1 day ago
Roundtrip flight included
Houston (HOU) to Albany (ALB)
Stay at this hotel in Lenox. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff in our reviews. Popular attractions Tanglewood Music Center and Lenox Library are located nearby.

Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
Price was $754, price is now $581 per person
$581
per person
Nov 10 - Nov 17
found 1 day ago
Roundtrip flight included
Houston (HOU) to Albany (ALB)
Book a stay at this family-friendly aparthotel in Williamstown. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions Jiminy Peak Mountain Resort and Mountain Coaster are located nearby.
Excellent customer service from front desk staff! Very nice decor everywhere. Fun little balcony! Quiet in the suite. All good!

Reviewed on Sep 3, 2026

Sleeps 40 Heated Pool Hot Tub Fire Pit Game Room Brookside Mountain Retreat by Avantstay

Sleeps 40 Heated Pool Hot Tub Fire Pit Game Room Brookside Mountain Retreat by Avantstay

3 out of 5
Save 100% on your flight
Price was $2,806, price is now $2,194 per person
$2,194
per person
Oct 27 - Oct 29
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Albany (ALB)
Stay at this cottage in Stephentown. Enjoy free parking, volleyball on site, and a pool table. Popular attractions Jiminy Peak Mountain Resort and Zema's Nursery are located nearby.

The Landing Hotel at Rivers Casino Schenectady

The Landing Hotel at Rivers Casino Schenectady

4 out of 5
Price was $694, price is now $544 per person
$544
per person
Nov 19 - Nov 22
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
Book a stay at this business-friendly hotel in Schenectady. Enjoy free WiFi, free parking, and 5 restaurants. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Rivers Casino & Resort and Schenectady Light Opera Performing Arts Center are located nearby.
Tranquilité des lieux, personnel très accueillant et très grande propreté des lieux

Reviewed on Aug 30, 2026

Saratoga Casino Hotel

Saratoga Casino Hotel

4 out of 5
Price was $1,138, price is now $895 per person
$895
per person
Oct 6 - Oct 11
found 18 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Albany (ALB)
Stay at this hotel in Saratoga Springs. Enjoy free WiFi, free parking, and a casino. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Saratoga Casino and Saratoga Racetrack are located nearby.

Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
Price was $723, price is now $569 per person
$569
per person
Nov 10 - Nov 17
found 1 day ago
Roundtrip flight included
Houston (HOU) to Albany (ALB)
Book a stay at this golf aparthotel in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Tanglewood Music Center and Guido's Marketplace are located nearby.
They really need to fix the hot tub, And they could use some new mattresses

Reviewed on Sep 3, 2026

Cheshire Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Lodges At Cresthaven

Lodges At Cresthaven

4 out of 5
Price was $641, price is now $471 per person
$471
per person
Nov 19 - Nov 22
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

3.5 out of 5
Save 100% on your flight
Price was $1,305, price is now $906 per person
$906
per person
Oct 22 - Oct 26
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
The Ponds at Foxhollow

The Ponds at Foxhollow

3 out of 5
Save 100% on your flight
Price was $956, price is now $695 per person
$695
per person
Oct 22 - Oct 26
found 2 days ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort

3.5 out of 5
Price was $841, price is now $628 per person
$628
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)

Cheshire Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort

3.5 out of 5
Price was $871, price is now $631 per person
$631
per person
Oct 22 - Oct 29
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

3.5 out of 5
Price was $1,199, price is now $842 per person
$842
per person
Nov 10 - Nov 17
found 1 day ago
Roundtrip flight included
Houston (HOU) to Albany (ALB)
The Whitlock

The Whitlock

2 out of 5
Save 100% on your flight
Price was $1,237, price is now $876 per person
$876
per person
Oct 22 - Oct 29
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
The Manchester View

The Manchester View

2.5 out of 5
Save 100% on your flight
Price was $2,584, price is now $1,938 per person
$1,938
per person
Oct 6 - Oct 11
found 23 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Albany (ALB)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Allegiant Air
Thu, Sep 17 - Sun, Sep 27
FLL
Fort Lauderdale - Hollywood Intl.
ALB
Albany Intl.
$136 Roundtrip, just found
$136
Roundtrip
just found
Select Allegiant Air flight, departing Thu, Sep 17 from Fort Lauderdale - Hollywood Intl. to Albany Intl., returning Sun, Sep 27, priced at $136 just found
Bargain Flight
Sat, Sep 26 - Tue, Sep 29
CLT
Charlotte-Douglas Intl.
ALB
Albany Intl.
$240 Roundtrip, found 1 day ago
$240
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Sat, Sep 26 from Charlotte-Douglas Intl. to Albany Intl., returning Tue, Sep 29, priced at $240 found 1 day ago
Bargain Flight
Tue, Sep 29 - Tue, Oct 6
LAX
Los Angeles Intl.
ALB
Albany Intl.
$304 Roundtrip, just found
$304
Roundtrip
just found
Select Bargain Flight flight, departing Tue, Sep 29 from Los Angeles Intl. to Albany Intl., returning Tue, Oct 6, priced at $304 just found
Bargain Flight
Thu, Oct 29 - Mon, Nov 9
DFW
Dallas-Fort Worth Intl.
ALB
Albany Intl.
$307 Roundtrip, found 2 days ago
$307
Roundtrip
found 2 days ago
Select Bargain Flight flight, departing Thu, Oct 29 from Dallas-Fort Worth Intl. to Albany Intl., returning Mon, Nov 9, priced at $307 found 2 days ago